Seymour Homes for Sale

Welcome to Seymour, Connecticut – a hidden gem nestled in the heart of New Haven County! Known for its small-town charm and vibrant community spirit, Seymour offers a delightful blend of picturesque landscapes and modern conveniences. With its rich history dating back to the 1800s, this quaint town is perfect for those seeking a serene lifestyle without sacrificing access to urban amenities.

Seymour boasts an array of recreational opportunities, including beautiful parks, scenic walking trails, and the stunning Housatonic River, which is perfect for fishing and kayaking. The town is also home to top-rated schools, making it an ideal choice for families. With a strong sense of community, residents enjoy various local events, farmers' markets, and seasonal festivals that bring everyone together.

For those considering a move to Seymour, you’ll be pleased to discover a diverse selection of homes for sale. From charming historic houses that exude character to modern family homes equipped with all the latest amenities, there’s something for everyone. Whether you’re looking for a cozy starter home or a spacious property to accommodate your growing family, Seymour’s real estate market has plenty of options to suit your needs.

Explore our listings today and find your dream home in Seymour, where the perfect blend of tranquility and community awaits! Embrace the opportunity to live in a town that offers both a peaceful retreat and easy access to the bustling cities of New Haven and Hartford. Your new beginning starts here!

Newest Seymour Homes for Sale

$499,900

3 Beds ⋅ 3 Baths ⋅ 24192058 MLS

Hard-to-find 1960s ranch offering timeless craftsmanship, solid construction, and the convenience of true single-level living. Set along quiet Mountain Road in Seymour, the home sits beautifully on a level, tree-lined lot that provides privacy from neighboring properties. Inside, the comfortable floor plan features hardwood floors, oil-fired hot water heat with cast-iron radiators, and a charming stone-front exterior that reflects the quality of its era. The cozy living room includes a bay window and corner fireplace, while the dining room offers another bay window and views of the fireplace. A generously sized kitchen, three well-proportioned bedrooms, and a primary suite with a private full bath provide both comfort and functionality. Thoughtful updates include central air conditioning, a newer roof, replacement windows, and a repointed chimney. The partially finished lower level offers additional space for entertaining, recreation, or hobbies. Step outside to enjoy the peaceful setting, all while being conveniently located near shopping, dining, parks, and major commuter routes. Whether you're just starting, downsizing, or looking for easy everyday living, this delightful home is one you won't want to miss.

125 Mountain Rd, Seymour

$319,900

4 Beds ⋅ 3 Baths ⋅ 24193191 MLS

Yesteryear and today all rolled into one! This older two-story home brings some charm, character and recent updates. (Furnace, oil tank 2023; hot water heater 2025; roof 2017) Second floor remodeled aprox. 12 yrs. ago, with 1/2 bath included! Full bath on first floor boasts striking stained glass window. House sold "as is" for informational purposes. Owner must find suitable housing. Another full bath located in walk-out unfinished basement ideal for possible in-law setup (or framed room first floor possible.) Framed room , with fireplace, (approx. 18x16) adjacent to kitchen ready for your imagination. Bring your plans and envision a bonus room (or in-law) on the main level! Some remodeling on first floor.

1 Second Ave, Seymour

$314,900

3 Beds ⋅ 2 Baths ⋅ 24190592 MLS

Move-in ready with more space than you would expect, this well-maintained home offers a flexible layout and convenient location. Inside, you'll find a large eat-in kitchen with access to the flat backyard and shed, giving you plenty of room for everyday living, entertaining, and extra storage. The main level features two well-sized bedrooms, a full bath, a spacious living room, and a formal dining room. A bright sunroom/breezeway at the front of the home adds even more usable space and is perfect for relaxing, a home office nook, or plant lovers. Upstairs offers an additional well-sized bedroom along with walk-in attic storage, providing extra flexibility and room to grow. The full basement adds even more value with additional storage space, a full bath, and a one-car garage bay. With public water, public sewer, and easy access to Route 8 and Route 67, this home offers a practical layout with the space and features to fit a variety of needs. HIGHEST AND BEST WEDNESDAY 7/22 12:00 PM

172 Cedar St, Seymour

$699,900

3 Beds ⋅ 3 Baths ⋅ 24191421 MLS

***Highest and Best due 7/21 at 5:00pm*** Enjoy scenic views, exceptional indoor-outdoor living, and a home designed for entertaining in this beautiful Seymour property. The heart of the home is a beautiful gourmet spacious kitchen featuring stainless steel appliances, and a unique gas-fired pizza oven, perfect for entertaining family and friends. The open-concept living and dining areas are filled with natural light and feature a stunning stone fireplace and large windows overlooking the surrounding landscape. The home offers comfortable living spaces, updated bathrooms, generous bedrooms, and flexible areas that can accommodate a home office, gym, or playroom. Step outside to an expansive deck overlooking the backyard, where you'll find an above-ground pool with pool house, beautifully maintained landscaping, and peaceful views that can be enjoyed year-round. Whether you're hosting gatherings, relaxing by the pool, or enjoying a quiet evening outdoors, this home offers the perfect setting. Owner is a licensed real estate agent.

70 N Benham Rd, Seymour

$360,000

3 Beds ⋅ 2 Baths ⋅ 24191775 MLS

Welcome to 169 Derby Avenue, a renovated three-bedroom Colonial offering direct frontage and peaceful views of the Naugatuck River. The bright and inviting main level features a comfortable living room, dining area, updated kitchen and convenient half bathroom. An additional sitting room provides flexible space for a home office, library, playroom or quiet retreat. Upstairs, you'll find three comfortable bedrooms and a full bathroom. The finished basement offers additional space for recreation, storage and laundry. Outside, enjoy a spacious deck and backyard overlooking the river-an appealing setting for relaxing, entertaining and taking in the changing seasons. Additional highlights include central air, zoned cooling, public water, public sewer, vinyl siding, a security system and private off-street parking at the end of the shared driveway. Conveniently located near downtown Seymour, shopping, restaurants, Route 8 and the Metro-North train station. A distinctive opportunity combining historic Colonial character, modern updates and scenic riverfront living.

169 Derby Ave, Seymour

$569,900

3 Beds ⋅ 3 Baths ⋅ 24191863 MLS

Welcome to your own private oasis, nestled on a lightly wooded lot at the end of a quiet cul de sac, this beautiful Colonial offers the perfect combination of privacy,space and convenience. Whether you are looking for a peaceful retreat or a home designed for entertaining, this property has it all. Ideally located just minutes from RT 8, you'll enjoy an easy commute both north and south while still feeling tucked away from the hustle and bustle.At the end of the street , Gary Park provides easy access to playgrounds, ball fields and outdoor recreation providing outdoor entertainment. Step inside to a warm and inviting floor plan designed for both every day living and many special occasions. The spacious kitchen opens seamlessly to the family room, creating the heart of the home. Large windows fill the space with natural light, while easy access s to the rear deck makes and indoor-outdoor entertaining effortless. Whether you are hosting summer cookouts, holiday gatherings or simply enjoying your morning coffee overlooking the private backyard, this home offers the perfect setting. For more formal occasions, the elegant living room and dining room low together beautifully, providing flexible space for entertaining guests or enjoying intimate dinners. Upstairs you'll find three generously sized bedrooms with beautiful hardwood flooring throughout,. The second and third bedrooms offer excellent closet space, the third bedroom featuring its own walk in closet.

32 Shari Dr, Seymour

$379,900

3 Beds ⋅ 2 Baths ⋅ 24190315 MLS

Welcome home to this well-maintained property set on a level lot in a convenient Seymour location. Inside, you'll find a bright, functional layout with inviting living spaces and generously sized bedrooms. Step outside to a spacious backyard with plenty of room to relax, entertain, or enjoy outdoor activities. Ideally situated just minutes from shopping, restaurants, parks, schools, and Route 8, this home offers the perfect blend of everyday convenience and neighborhood charm.

105 Walnut St, Seymour

$879,000

4 Beds ⋅ 3 Baths ⋅ 24189353 MLS

Classic 4 bedroom, 2 and a half bath home nearing completion. This home features a large eat-in country kitchen with granite countertops and a large center island, opening up to spacious family room with gas fireplace. French doors provide access to the deck over-looking the backyard and a private undeveloped area, in addition to the wrap-around front porch at overlooks the private front and side yard The connection to the dining room offers a small butler's pantry for ease and convenience for entertaining. Access into the home from the 2-car garage is through a large mud-room and an adjacent half bath. There is another deck off of the back of the mudroom. Upstairs there is a large MBR with a sitting area, generous master bath and 2 walk-in closets with a dressing room. The other 3 bedrooms all feature walk-in closets and share a hall bath with a double sink. The laundry is also located upstairs and features a large tub, as well as the washer and dryer. The pull-down stairs to the attic is also located in the laundry room The enormous (in excess of 1000 sf) walk-out lower level is finished and has sliders to a patio in the backyard.

4 Mead Farm Rd, Seymour

$580,000

3 Beds ⋅ 3 Baths ⋅ 24185980 MLS

Welcome to this custom-built contemporary home featuring quality 2x6 construction and beautiful hardwood flooring throughout. Nestled in a private, peaceful setting, the exterior features an impressive 60-foot back deck designed for entertaining, plus two sheds (one powered and ready for a pool setup!). Inside, the spacious kitchen is a chef's delight with endless Corian countertops and a second wall oven. Major updates provide peace of mind, including all-new windows and a basement slider (2023), plus a newer roof (2018). Stay cozy with a pellet stove in the living room and a propane fireplace in the lower-level family room. The unfinished basement area offers incredible workshop or storage potential. Settled in a great neighborhood! See attached for a complete list of highlights and upgrades.

15 Briarwood Dr, Seymour

$475,000

5 Beds ⋅ 2 Baths ⋅ 24189350 MLS

Spacious 5-Bedroom Home on a Premium 2.25-Acre Lot! Offering incredible space and versatility, this unique property features 4 upper-level bedrooms and a 5th bedroom on the walk-out lower level-perfect for extended family or guests. Step inside to find classic hardwood floors throughout the living room and bedrooms, charming knotty pine accents, and a sealed fireplace waiting for your personal touch. The heart of the home features an extra-large addition dining room, ideal for hosting large gatherings. Recent updates include a fully renovated full bath (2023), ceiling lights in the rooms, a newer 10-yr +/- roof, and a brand-new water pump (2024). All appliances, including the basement washer and dryer, are included! Mechanically, the home is equipped with central air (older AC unit), oil hot water heat (dual furnaces/dual tanks; note: one tank needs replacement), and a solid main house block foundation. The property serviced by well and septic. Eco-conscious buyers will appreciate the solar panels (lease to be assumed). The exterior is an absolute standout for car enthusiasts, hobbyists, or homesteaders! It boasts an attached 2-car garage, an additional rear-entrance 1-car maintenance garage, and a chicken coop ready for use on the expansive 2.25-acre grounds. With a walk-out lower level and endless potential, this property is being sold as-is and is ready for your vision. Subject to seller finding and closing on home of choice.

67 Botsford Rd, Seymour

$499,900

4 Beds ⋅ 3 Baths ⋅ 24155474 MLS

2 HOUSES IN ONE!! INLAW, IN LAW SUITE... Step inside this 11-room, 4-5 bedroom home with In-Law apartment on a prime corner lot!! Hardwood floors and cool breeze of central air conditioning. This house offers space for everyone, including a full in-law apartment perfect for extended family. Downstairs, you will find a spacious two-car garage. Lots of Storage!! Floored Walk-Up Attic. Great Workshop space for your next project, BRING YOUR TALENTS.. Private patio for relaxing barbecues (Roof needs repair). The location is truly unbeatable steps away from the fun at Legion Pond Park, one block close to Chatfield-LoPresti Elementary School. Easy commuting, shopping, local restaurants, and major highways. Perfect blend of space, comfort, and convenience. Subject to Probate Approval.

30 Bunting Rd, Seymour

$449,900

4 Beds ⋅ 3 Baths ⋅ 24188026 MLS

Welcome to 123 Pearl Street - a breathtaking Victorian-style residence in the heart of Seymour, where timeless architectural charm meets modern luxury living. This magnificent home has been thoughtfully and completely updated / remodeled throughout, preserving its original character while offering every contemporary comfort today's owner expects. From the moment you arrive, the steeply pitched rooflines, ornate gingerbread trim, and inviting front porch announce the home's Victorian heritage. Step inside to discover soaring ceilings, rich millwork, beautiful turret and light-filled rooms that flow seamlessly for both everyday living and elegant entertaining. All the amenities of modern living with the charm of a classic Victorian. Bedrooms are all generous in size and the the home has a beautiful primary bedroom suite with an large bathroom and walk-in closet space. Potential: This home offers excellent two-family conversion potential - a rare opportunity for investors, multi-generational families, or buyers seeking rental income to offset their mortgage. Conveniently located with easy access to major commuter routes, train and downtown - this is the rare home that truly has it all. Seller is an agent

123 Pearl St, Seymour

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